I currently work in software and would love to leverage some of my automation skills to streamline repetitive tasks related to real estate investing (if there are any!). 

The first thing you need to invest in is yourself... read every real estate book you can get your hands on until they start to sound repetitive. 

It’s not nice, but if you find out the property is a money pit, use the inspection clause provisions (I assume in your contracts you have one..) to get out the deal.See how there is a phased, repetitive approach to this?

The message gets weaker with every repetition.

I’m thinking about posting an ad on Upwork and seeing if I can find someone to handle the repetitive computer and phone work tasks virtually.  

Hi @David Carpenter the short answer is "reps" . . . repetition will build an intuition in this and be an ally. 

Hi,I'm trying to get my repetitions up underwriting mock apartment scenarios. 

We want a magic pill because all the things that work well are boring and repetitive.

There's something to be said for this, as those "good opportunities" get you repetitions that lead to clarity and skill growth, so they are not to be avoided, but if you see yourself owning property for a few decades and have the budget for it now I'd look for things that cashflow well in good areas on normal lots (i.e. not too small, not too shallow, but just right)

I've had the same repetitive conversation with her countless times:  that she knows I'll work with her, but I can't work in a vacuum and she will promptly get a notice every, single time she ignores me.